Questions

The stability of the ions is determined by the energy of the lone pairs. Carbon has the least effective nuclear charge (Zeff) and so the lone pair on the CH3− ion has the highest energy, making it the least stable ion and so the strongest base. The Zeff increases as we move across the period until we get to fluorine which has the greatest Zeff and so its lone pairs have the lowest energy, making F− the least basic ion.

In order of decreasing basicity they are ranked LiCH3 > LiNH2 > LiOH > LiF. We are dealing with the ions F−, OH−, NH2− and CH3− and so the factor which influences their basicity is the stability of the ion compared to its conjugate acid.

The order of basicity in ammonia is different in gaseous phases vs. aqueous phases due to hydrogen bonding.

So in gaseous phases it's the well known: 3' > 2' > 1'> NH3. Just so we're on the same page, this is due to the inductive effect of electron donating alkyl groups--they destabilize the lone pair on nitrogen atom, making nitrogen more basic.

But in aqueous phase, the order is slightly different: 2'> 1'> 3' > NH3.

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